原创力文档the reaction of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophenes with benzoyl-isothiocyanate synthesis of annulated thiophene derivatives and their antitumor evaluations英文论文.pdfVIP
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the reaction of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophenes with benzoyl-isothiocyanate synthesis of annulated thiophene derivatives and their antitumor evaluations英文论文
International Journal of Organic Chemistry, 2012, 2, 126-134
/ 10.4236/ijoc.2012.22020 Published Online June 2012 (http://www.SciRP.org/journal/ijoc)
The Reaction of
2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophenes with
Benzoyl-Isothiocyanate: Synthesis of Annulated
Thiophene Derivatives and Their Antitumor Evaluations
1* 2 3
Karam Ahmed El-Sharkawy , Hend Mohamed El-Sehrawi , Rehab Ali Ibrahim
1Department of Organic Chemistry, Faculty of Pharmacy, October University for Modern Sciences
and Arts, 6th of October City, Egypt
2Pharmaceutical Chemistry Department, Faculty of Pharmacy (Girls), Al-Azhar University, Nasr City, Cairo, Egypt
3Higher Institute of Engineering and Technology, El-Tagammoe El-Khames, New Cairo, Egypt
*
Email: karamsyn@
Received April 10, 2012; revised May 12, 2012; accepted May 17, 2012
ABSTRACT
The reaction of the tetrahydrobenzo[b]thiophene derivatives 1a,b with benzoylisothiocyanate (2) afforded the thiourea
derivatives 3a,b. Cyclization of the latter products gave the annulated products 4a,b. Compounds 3a,b reacted with ei-
ther hydrazine hydrate (5a) or phenyl hydrazine (5b) afforded compounds 7a-d which underwent cyclization for com-
pounds 7a,c afforded compound 9. On the other hand compounds 4a,b reacted with either hydrazine hydrate (5a) or
phenyl hydrazine (5b) afforded compounds 6a-d a second pathway was applied to synthesize compound 6c which un-
derwent cyclization afforded compound 9. Also compounds 4a,b reacted with either phenacyl bromide (10) a
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